Fluvoxamine

Identification

Summary

Fluvoxamine is a selective serotonin-reuptake inhibitor used to treat obsessive-compulsive disorder.

Brand Names
Luvox
Generic Name
Fluvoxamine
DrugBank Accession Number
DB00176
Background

Fluvoxamine is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. Though it is in the same class as other SSRI drugs, it is most often used to treat obsessive-compulsive disorder. Fluvoxamine has been in use in clinical practice since 1983 and has a clinical trial database comprised of approximately 35,000 patients. It was launched in the US in December 1994 and in Japan in June 1999. As of the end of 1995, more than 10 million patients worldwide have been treated with fluvoxamine.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 318.34
Monoisotopic: 318.155512413
Chemical Formula
C15H21F3N2O2
Synonyms
  • Fluvoxamina
  • Fluvoxamine
  • Fluvoxaminum

Pharmacology

Indication

Indicated predominantly for the management of depression and for Obsessive Compulsive Disorder (OCD) Label. Has also been used in the management of bulimia nervosa 2.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Fluvoxamine, an aralkylketone-derivative agent Label, is one of a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs) that differs structurally from other SSRIs 1. It is used to treat the depression associated with mood disorders. It is also used on occassion in the treatment of body dysmorphic disorder and anxiety 1. The antidepressant, antiobsessive-compulsive, and antibulimic actions of Fluvoxamine are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin Label,1,2. In vitro studies show that Fluvoxamine is a potent and selective inhibitor of neuronal serotonin reuptake and has only very weak effects on norepinephrine and dopamine neuronal reuptake 2. Moreover, apart from binding to σ1 receptors 2, fluvoxamine has no significant affinity for adrenergic (alpha1, alpha2, beta), cholinergic, GABA, dopaminergic, histaminergic, serotonergic (5HT1A, 5HT1B, 5HT2), or benzodiazepine receptors; antagonism of such receptors has been hypothesized to be associated with various anticholinergic, sedative, and cardiovascular effects for other psychotropic drugs 1. Furthermore, some studies have demonstrated that the chronic administration of Fluvoxamine was found to downregulate brain norepinephrine receptors (as has been observed with other drugs effective in the treatment of major depressive disorder), while others suggest the opposite 3.

Mechanism of action

The exact mechanism of action of fluvoxamine has not been fully determined, but appears to be linked to its inhibition of CNS neuronal uptake of serotonin Label,1,2. Fluvoxamine blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT1A autoreceptors Label,1,2. Studies have also demonstrated that fluvoxamine has virtually no affinity for α1- or α2-adrenergic, β-adrenergic, muscarinic, dopamine D2, histamine H1, GABA-benzodiazepine, opiate, 5-HT1, or 5-HT2 receptors, despite having an affinity for binding to σ1 receptors 2.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Humans
UPotassium voltage-gated channel subfamily H member 2Not AvailableHumans
Absorption

Well absorbed, bioavailability of fluvoxamine maleate is 53% Label.

Volume of distribution
Protein binding

~77-80% (plasma protein) Label.

Metabolism

Fluvoxamine is metabolized extensively by the liver Label.

Hover over products below to view reaction partners

Route of elimination

Nine metabolites were identified following a 5 mg radio labelled dose of fluvoxamine maleate, constituting approximately 85% of the urinary excretion products of fluvoxamine Label. The main human metabolite was fluvoxamine acid which, together with its N-acetylated analog, accounted for about 60% of the urinary excretion products Label. Approximately 2% of fluvoxamine was excreted in urine unchanged Label. Following a 14C-labelled oral dose of fluvoxamine maleate (5 mg), an average of 94% of drug-related products was recovered in the urine within 71 hours Label.

Half-life

15.6 hours Label.

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Fluvoxamine is a member of antidepressants that possess an increased risk compared to placebo of suicidal thinking and behaviour (suicidality) in children, adolescents, and young adults (ages including and and below 24) in short-term studies of major depressive disorder and other psychiatric disorders Label.

Fluvoxamine maleate tablets are not approved for use in pediatric patients except for patients with obsessive compulsive disorder (OCD) Label.

Side effects include anorexia, constipation, dry mouth, headache, nausea, nervousness, skin rash, sleep problems, somnolence, liver toxicity, mania, increase urination, seizures, sweating increase, tremors, or Tourette's syndrome Label.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2D6CYP2D6*3Not Available2549delAEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of fluvoxamine.Details
Cytochrome P450 2D6CYP2D6*4Not AvailableA alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of fluvoxamine.Details
Cytochrome P450 2D6CYP2D6*5Not AvailableWhole-gene deletionEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of fluvoxamine.Details
Cytochrome P450 2D6CYP2D6*6Not Available1707delTEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of fluvoxamine.Details
Cytochrome P450 2D6CYP2D6*7Not Available2935A>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*8Not Available1758G>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*11Not Available883G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*12Not Available124G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*13Not AvailableCYP2D7/2D6 hybrid gene structureEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*14ANot Available1758G>AEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*15Not Available137insT, 137_138insTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*19Not Available2539_2542delAACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*20Not Available1973_1974insGEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*21Not Available2573insCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*31Not Available-1770G>A / -1584C>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*36Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*38Not Available2587_2590delGACTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*40Not Available1863_1864ins(TTT CGC CCC)2Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*42Not Available3259_3260insGTEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*44Not Available2950G>CEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*47Not Available100C>T / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*51Not Available-1584C>G / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*56Not Available3201C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*57Not Available100C>T / 310G>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*62Not Available4044C>TEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68ANot Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*68BNot AvailableSimilar but not identical switch region compared to CYP2D6*68A. Found in tandem arrangement with CYP2D6*4.Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*69Not Available2988G>A / -1426C>T  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*92Not Available1995delCEffect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*100Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*101Not Available-1426C>T / -1235A>G  … show all Effect InferredPoor drug metabolizer. For individual with two non-functional alleles, alternative drug or dose reduction recommended.Details
Cytochrome P450 2D6CYP2D6*3Not AvailableG alleleEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of fluvoxamine.Details
Cytochrome P450 2D6CYP2D6*4Not Available3877G>AEffect Directly StudiedThe presence of this polymorphism in CYP2D6 is associated with reduced or poor metabolism of fluvoxamine.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Fluvoxamine.
AbacavirFluvoxamine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Fluvoxamine.
AbametapirThe serum concentration of Fluvoxamine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Fluvoxamine can be increased when combined with Abatacept.
AbciximabThe risk or severity of hemorrhage can be increased when Fluvoxamine is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Fluvoxamine.
AbirateroneThe serum concentration of Fluvoxamine can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Fluvoxamine.
AcarboseThe risk or severity of hypoglycemia can be increased when Fluvoxamine is combined with Acarbose.
Interactions
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Food Interactions
  • Avoid alcohol.
  • Avoid grapefruit products.
  • Limit caffeine intake.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fluvoxamine maleate5LGN83G74V61718-82-9LFMYNZPAVPMEGP-PIDGMYBPSA-N
Product Images
International/Other Brands
Dumirox (Abbott) / Faverin (Abbott) / Fevarin (Abbott) / Floxyfral (Abbott) / Maveral (Abbott)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act FluvoxamineTablet100 mgOralTEVA Canada Limited2004-08-13Not applicableCanada flag
Act FluvoxamineTablet50 mgOralTEVA Canada Limited2004-08-13Not applicableCanada flag
Bci Fluvoxamine TabletsTablet50.0 mgOralBaker Cummins Inc2005-07-042006-10-03Canada flag
Bci Fluvoxamine TabletsTablet100.0 mgOralBaker Cummins Inc2005-07-042006-10-03Canada flag
FluvoxamineTablet100 mgOralApotex Corporation1998-10-30Not applicableCanada flag
FluvoxamineTablet50 mgOralApotex Corporation1998-10-30Not applicableCanada flag
Fluvoxamine MaleateTablet100 mg/1OralRemedy Repack2013-09-112013-09-12US flag
Fluvoxamine MaleateTablet25 mg/1OralBayPharma, Inc.2008-01-252013-12-31US flag42769 122220180907 15195 2e1wer
Fluvoxamine maleateTablet, film coated50 mg/1OralSynthon Pharmaceuticals, Inc.2007-09-20Not applicableUS flag
Fluvoxamine MaleateTablet100 mg/1OralBayPharma, Inc.2008-01-252013-12-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-fluvoxamine TabletsTablet50 mgOralApotex Corporation1997-05-20Not applicableCanada flag
Apo-fluvoxamine TabletsTablet100 mgOralApotex Corporation1998-05-20Not applicableCanada flag
Ava-fluvoxamineTablet100 mgOralAvanstra Inc2011-08-222014-08-21Canada flag
Ava-fluvoxamineTablet50 mgOralAvanstra Inc2011-08-222014-08-21Canada flag
Dom-fluvoxamineTablet100 mgOralDominion Pharmacal2000-02-232016-10-25Canada flag
Dom-fluvoxamineTablet50 mgOralDominion Pharmacal2000-02-232016-10-25Canada flag
Fluvoxamine MaleateTablet, coated25 mg/1OralANI Pharmaceuticals, Inc.2011-08-09Not applicableUS flag62559 0158 01 nlmimage10 313b98dc
Fluvoxamine MaleateTablet, film coated100 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-03-12Not applicableUS flag
Fluvoxamine MaleateTablet, film coated100 mg/1OralBarr Laboratories2001-01-252013-10-31US flag0555 096920180907 15195 gl5p2a
Fluvoxamine MaleateTablet, coated100 mg/1Oralbryant ranch prepack2011-08-09Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FAVERIN 100 MG TABLET, 30 ADETFluvoxamine (100 mg)TabletOralABBOTT LABORATUARLARI İTHALAT İHRACAT VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
N06AB08 — Fluvoxamine
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
O4L1XPO44W
CAS number
54739-18-3
InChI Key
CJOFXWAVKWHTFT-XSFVSMFZSA-N
InChI
InChI=1S/C15H21F3N2O2/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18/h5-8H,2-4,9-11,19H2,1H3/b20-14+
IUPAC Name
(E)-(2-aminoethoxy)({5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene})amine
SMILES
COCCCC\C(=N/OCCN)C1=CC=C(C=C1)C(F)(F)F

References

Synthesis Reference

Welle, H.B.A. and Claassen, V.; U.S. Patent 4,085,225; April 18, 1978; assigned to U.S. Phillips Corp.

General References
  1. Dell'Osso B, Allen A, Hollander E: Fluvoxamine: a selective serotonin re-uptake inhibitor for the treatment of obsessive-compulsive disorder. Expert Opin Pharmacother. 2005 Dec;6(15):2727-40. [Article]
  2. Irons J: Fluvoxamine in the treatment of anxiety disorders. Neuropsychiatr Dis Treat. 2005 Dec;1(4):289-99. [Article]
  3. Foster RH, Goa KL: Paroxetine : a review of its pharmacology and therapeutic potential in the management of panic disorder. CNS Drugs. 1997 Aug;8(2):163-88. doi: 10.2165/00023210-199708020-00010. [Article]
KEGG Compound
C07571
PubChem Compound
3404
PubChem Substance
46507588
ChemSpider
4481878
BindingDB
50028091
RxNav
42355
ChEBI
5138
ChEMBL
CHEMBL814
ZINC
ZINC000003872605
Therapeutic Targets Database
DNC000897
PharmGKB
PA449690
PDBe Ligand
FVX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Fluvoxamine
PDB Entries
4enh / 4mm9 / 6awp
FDA label
Download (633 KB)
MSDS
Download (48.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS1
4CompletedTreatmentDepressive Disorder, Recurrent1
4CompletedTreatmentMajor Depressive Disorder (MDD)2
4CompletedTreatmentObsessive Compulsive Disorder (OCD)1
4CompletedTreatmentSchizophrenia1
4Not Yet RecruitingTreatmentMajor Depressive Disorder (MDD)1
4RecruitingTreatmentDepressive Disorders1
4RecruitingTreatmentObsessive Compulsive Disorder (OCD)1
4TerminatedTreatmentObsessive Compulsive Disorder (OCD)1
4Unknown StatusNot AvailableBreast Milk Production / Depressive Disorders1

Pharmacoeconomics

Manufacturers
  • Jazz pharmaceuticals
  • Actavis elizabeth llc
  • Apotex inc
  • Barr laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Sandoz inc
  • Synthon pharmaceuticals ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Ani pharmaceuticals inc
  • Solvay pharmaceuticals
Packagers
  • Anip Acquisition Co.
  • Apotex Inc.
  • Barr Pharmaceuticals
  • Bay Pharma Inc.
  • Caraco Pharmaceutical Labs
  • Elan Pharmaceuticals Inc.
  • Eon Labs
  • Excella GmbH
  • Golden State Medical Supply Inc.
  • Heartland Repack Services LLC
  • Ivax Pharmaceuticals
  • Jazz Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Resource Optimization and Innovation LLC
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Synthon Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Torpharm Inc.
  • UDL Laboratories
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
Tablet, delayed releaseOral
TabletOral100.0 mg
TabletOral50.0 mg
Tablet, film coatedOral100 mg
TabletOral
Tablet, film coatedOral50 mg
Tablet, delayed releaseOral100 MG
Tablet, film coatedOral
TabletOral100 MG
Capsule, extended releaseOral100 mg/1
Capsule, extended releaseOral150 mg/1
TabletOral100 mg/1
TabletOral25 mg/1
TabletOral50 mg/1
Tablet, coatedOral100 mg/1
Tablet, coatedOral25 mg/1
Tablet, coatedOral50 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral25 mg/1
Tablet, film coatedOral50 mg/1
Tablet, coatedOral100 mg
Tablet, coatedOral50 mg
TabletOral50 mg
TabletOral100 mg / tab
TabletOral50 mg / tab
Prices
Unit descriptionCostUnit
Luvox CR 150 mg 24 Hour Capsule6.34USD capsule
Luvox cr 150 mg capsule6.24USD capsule
Luvox CR 100 mg 24 Hour Capsule6.05USD capsule
Luvox cr 100 mg capsule5.82USD capsule
Fluvoxamine maleate 100 mg tablet2.69USD tablet
Fluvoxamine mal 100 mg tablet2.63USD tablet
Fluvoxamine maleate 50 mg tablet2.61USD tablet
Fluvoxamine maleate 25 mg tablet2.34USD tablet
Luvox 100 mg Tablet1.7USD tablet
Luvox 50 mg Tablet0.95USD tablet
Apo-Fluvoxamine 100 mg Tablet0.93USD tablet
Co Fluvoxamine 100 mg Tablet0.93USD tablet
Novo-Fluvoxamine 100 mg Tablet0.93USD tablet
Nu-Fluvoxamine 100 mg Tablet0.93USD tablet
Pms-Fluvoxamine 100 mg Tablet0.93USD tablet
Ratio-Fluvoxamine 100 mg Tablet0.93USD tablet
Sandoz Fluvoxamine 100 mg Tablet0.93USD tablet
Apo-Fluvoxamine 50 mg Tablet0.52USD tablet
Co Fluvoxamine 50 mg Tablet0.52USD tablet
Novo-Fluvoxamine 50 mg Tablet0.52USD tablet
Nu-Fluvoxamine 50 mg Tablet0.52USD tablet
Pms-Fluvoxamine 50 mg Tablet0.52USD tablet
Ratio-Fluvoxamine 50 mg Tablet0.52USD tablet
Sandoz Fluvoxamine 50 mg Tablet0.52USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7465462No2008-12-162020-05-10US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120-121.5 °CWelle, H.B.A. and Claassen, V.; U.S. Patent 4,085,225; April 18, 1978; assigned to U.S. Phillips Corp.
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00734 mg/mLALOGPS
logP2.89ALOGPS
logP2.8ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area56.84 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity79.2 m3·mol-1ChemAxon
Polarizability32.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9775
Caco-2 permeable-0.5149
P-glycoprotein substrateSubstrate0.6079
P-glycoprotein inhibitor IInhibitor0.7883
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.5325
CYP450 2C9 substrateNon-substrate0.8595
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateNon-substrate0.6723
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8481
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.637
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6997 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8427
hERG inhibition (predictor II)Inhibitor0.7995
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Kakiuchi T, Tsukada H, Fukumoto D, Nishiyama S: Effects of aging on serotonin transporter availability and its response to fluvoxamine in the living brain: PET study with [(11)C](+)McN5652 and [(11)C](-)McN5652 in conscious monkeys. Synapse. 2001 Jun 1;40(3):170-9. [Article]
  2. Yoshida K, Ito K, Sato K, Takahashi H, Kamata M, Higuchi H, Shimizu T, Itoh K, Inoue K, Tezuka T, Suzuki T, Ohkubo T, Sugawara K, Otani K: Influence of the serotonin transporter gene-linked polymorphic region on the antidepressant response to fluvoxamine in Japanese depressed patients. Prog Neuropsychopharmacol Biol Psychiatry. 2002 Feb;26(2):383-6. [Article]
  3. Miolo G, Caffieri S, Levorato L, Imbesi M, Giusti P, Uz T, Manev R, Manev H: Photoisomerization of fluvoxamine generates an isomer that has reduced activity on the 5-hydroxytryptamine transporter and does not affect cell proliferation. Eur J Pharmacol. 2002 Aug 30;450(3):223-9. [Article]
  4. Suhara T, Takano A, Sudo Y, Ichimiya T, Inoue M, Yasuno F, Ikoma Y, Okubo Y: High levels of serotonin transporter occupancy with low-dose clomipramine in comparative occupancy study with fluvoxamine using positron emission tomography. Arch Gen Psychiatry. 2003 Apr;60(4):386-91. [Article]
  5. Inoue K: [Analysis and its application for prevention of side-effects of drugs and for evaluation of drug responsiveness]. Yakugaku Zasshi. 2004 Jun;124(6):293-9. [Article]
  6. McMahon LR, Cunningham KA: Role of 5-HT(2a) and 5-HT(2B/2C) receptors in the behavioral interactions between serotonin and catecholamine reuptake inhibitors. Neuropsychopharmacology. 2001 Mar;24(3):319-29. [Article]
  7. Millan MJ, Veiga S, Girardon S, Brocco M: Blockade of serotonin 5-HT1B and 5-HT2A receptors suppresses the induction of locomotor activity by 5-HT reuptake inhibitors, citalopram and fluvoxamine, in NMRI mice exposed to a novel environment: a comparison to other 5-HT receptor subtypes. Psychopharmacology (Berl). 2003 Aug;168(4):397-409. Epub 2003 Apr 30. [Article]
  8. Dell'Osso B, Allen A, Hollander E: Fluvoxamine: a selective serotonin re-uptake inhibitor for the treatment of obsessive-compulsive disorder. Expert Opin Pharmacother. 2005 Dec;6(15):2727-40. [Article]
  9. Irons J: Fluvoxamine in the treatment of anxiety disorders. Neuropsychiatr Dis Treat. 2005 Dec;1(4):289-99. [Article]
  10. Williams K, Wheeler DM, Silove N, Hazell P: Selective serotonin reuptake inhibitors (SSRIs) for autism spectrum disorders (ASD). Cochrane Database Syst Rev. 2010 Aug 4;(8):CD004677. doi: 10.1002/14651858.CD004677.pub2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Friemel A, Zunkler BJ: Interactions at human ether-a-go-go-related gene channels. Toxicol Sci. 2010 Apr;114(2):346-55. doi: 10.1093/toxsci/kfq011. Epub 2010 Jan 13. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
  2. Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [Article]
  3. Ozdemir V, Naranjo CA, Shulman RW, Herrmann N, Sellers EM, Reed K, Kalow W: Determinants of interindividual variability and extent of CYP2D6 and CYP1A2 inhibition by paroxetine and fluvoxamine in vivo. J Clin Psychopharmacol. 1998 Jun;18(3):198-207. [Article]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Rasmussen BB, Nielsen TL, Brosen K: Fluvoxamine is a potent inhibitor of the metabolism of caffeine in vitro. Pharmacol Toxicol. 1998 Dec;83(6):240-5. [Article]
  2. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
  3. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [Article]
  4. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [Article]
  5. Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [Article]
  6. Yasui-Furukori N, Inoue Y, Kaneko S, Otani K: Determination of fluvoxamine and its metabolite fluvoxamino acid by liquid-liquid extraction and column-switching high-performance liquid chromatography. J Pharm Biomed Anal. 2005 Feb 7;37(1):121-5. [Article]
  7. Carrillo JA, Dahl ML, Svensson JO, Alm C, Rodriguez I, Bertilsson L: Disposition of fluvoxamine in humans is determined by the polymorphic CYP2D6 and also by the CYP1A2 activity. Clin Pharmacol Ther. 1996 Aug;60(2):183-90. doi: 10.1016/S0009-9236(96)90134-4. [Article]
  8. Flockhart Table of Drug Interactions [Link]
  9. Fluvoxamine FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Rasmussen BB, Maenpaa J, Pelkonen O, Loft S, Poulsen HE, Lykkesfeldt J, Brosen K: Selective serotonin reuptake inhibitors and theophylline metabolism in human liver microsomes: potent inhibition by fluvoxamine. Br J Clin Pharmacol. 1995 Feb;39(2):151-9. doi: 10.1111/j.1365-2125.1995.tb04422.x. [Article]
  2. Sy SK, Tang BK, Pastrakuljic A, Roberts EA, Kalow W: Detailed characterization of experimentally derived human hepatic CYP1A1 activity and expression using differential inhibition of ethoxyresorufin O-deethylation by fluvoxamine. Eur J Clin Pharmacol. 2001 Aug;57(5):377-86. doi: 10.1007/s002280100330. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
  2. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [Article]
  3. von Moltke LL, Greenblatt DJ, Duan SX, Harmatz JS, Wright CE, Shader RI: Inhibition of terfenadine metabolism in vitro by azole antifungal agents and by selective serotonin reuptake inhibitor antidepressants: relation to pharmacokinetic interactions in vivo. J Clin Psychopharmacol. 1996 Apr;16(2):104-12. [Article]
  4. van Harten J: Overview of the pharmacokinetics of fluvoxamine. Clin Pharmacokinet. 1995;29 Suppl 1:1-9. doi: 10.2165/00003088-199500291-00003. [Article]
  5. Flockhart Table of Drug Interactions [Link]
  6. FDA label, fluvoxamine [Link]
  7. Drug Interactions & Labeling - FDA [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...

Components:
References
  1. Rasmussen BB, Maenpaa J, Pelkonen O, Loft S, Poulsen HE, Lykkesfeldt J, Brosen K: Selective serotonin reuptake inhibitors and theophylline metabolism in human liver microsomes: potent inhibition by fluvoxamine. Br J Clin Pharmacol. 1995 Feb;39(2):151-9. doi: 10.1111/j.1365-2125.1995.tb04422.x. [Article]
  2. Flockhart Table of Drug Interactions [Link]
  3. Drug Interactions & Labeling - FDA [Link]
Details
6. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Micallef J, Fakra E, Blin O: [Use of antidepressant drugs in schizophrenic patients with depression]. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9. [Article]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  3. Madsen H, Enggaard TP, Hansen LL, Klitgaard NA, Brosen K: Fluvoxamine inhibits the CYP2C9 catalyzed biotransformation of tolbutamide. Clin Pharmacol Ther. 2001 Jan;69(1):41-7. doi: 10.1067/mcp.2001.112689. [Article]
  4. Hemeryck A, De Vriendt C, Belpaire FM: Inhibition of CYP2C9 by selective serotonin reuptake inhibitors: in vitro studies with tolbutamide and (S)-warfarin using human liver microsomes. Eur J Clin Pharmacol. 1999 Feb;54(12):947-51. [Article]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [Article]
  2. Yasui-Furukori N, Takahata T, Nakagami T, Yoshiya G, Inoue Y, Kaneko S, Tateishi T: Different inhibitory effect of fluvoxamine on omeprazole metabolism between CYP2C19 genotypes. Br J Clin Pharmacol. 2004 Apr;57(4):487-94. doi: 10.1111/j.1365-2125.2003.02047.x. [Article]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [Article]
  2. Hesse LM, Venkatakrishnan K, Court MH, von Moltke LL, Duan SX, Shader RI, Greenblatt DJ: CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants. Drug Metab Dispos. 2000 Oct;28(10):1176-83. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [Article]
  2. Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 18, 2021 04:56